Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed cyclic compound represented by Formula 1: 
     
       
         
         
             
             
         
       
     
     wherein, in Formula 1, rings, groups and variables are the same as defined in the specification.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0123657, filed on Sep. 1, 2015, and KoreanPatent Application No. 10-2015-0089087, filed on Jun. 23, 2015 in theKorean Intellectual Property Office, the content of which areincorporated herein in their entirety by reference.

BACKGROUND

1. Field

The present disclosure relates to a condensed cyclic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs exhibit high brightness, driving voltage,and response speed characteristics, and produce full-color images.

A typical organic light-emitting device includes an anode, a cathode,and an organic layer that is disposed between the anode and the cathode,wherein the organic layer includes an emission layer. A hole transportregion may be disposed between the anode and the emission layer, and anelectron transport region may be disposed between the emission layer andthe cathode. Holes provided from the anode may move toward the emissionlayer through the hole transport region, and electrons provided from thecathode may move toward the emission layer through the electrontransport region. Carriers, such as holes and electrons, are recombinedin the emission layer to produce excitons. These excitons change from anexcited state to a ground state, thereby generating light.

Different types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Provided are a novel condensed cyclic compound and an organiclight-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented exemplary embodiments.

According to an aspect of an exemplary embodiment, a condensed cycliccompound is represented by Formula 1:

wherein, in Formula 1,

X₁ is N or C(R₁), X₂ is N or C(R₂), X₃ is N or C(R₃), X₄ is N or C(R₄),X₅ is N or C(R₅), X₆ is N or C(R₆), X₇ is N or C(R₇), X₁₁ is N orC(R₁₁), X₁₂ is N or C(R₁₂), X₁₃ is N or C(R₁₃), X₁₄ is N or C(R₁₄), X₁₅is N, C(R₁₅), or a carbon atom connected to *-(L₁)_(a1)-*′, X₁₆ is N,C(R₁₆), or a carbon atom connected to *-(L₁)_(a1)-*′, X₁₇ is N, C(R₁₇),or a carbon atom connected to *-(L₁)_(a1)-*′, and X₁₈ is N, C(R₁₈), or acarbon atom connected to *-(L₁)_(a1)-*′, wherein one of X₁₅ to X₁₈ isconnected to *-(L₁)_(a1)-*′,

ring A₁ and ring A₂ are each independently selected from a C₅-C₆₀carbocyclic group and a C₃-C₆₀ heterocyclic group including at least oneheteroatom selected from O, S, and Si,

L₁ to L₃ are each independently selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group, a triazinylene group, afluorenylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and a phenylene group, a pyridinylene group,a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, atriazinylene group, a fluorenylene group, a dibenzofuranylene group, anda dibenzothiophenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃),

a1 to a3 are each independently an integer selected from 0 to 5, whereinwhen a1 is 2 or greater, two or more groups L₁ are identical to ordifferent from each other, when a2 is 2 or greater, two or more groupsL₂ are identical to or different from each other, and when a3 is 2 orgreater, two or more groups L₃ are identical to or different from eachother,

R₁ to R₇, R₁₁ to R₁₈, R₃₁, and R₃₂ are each independently selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup (CN), a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and —Si(Q₁)(Q₂)(Q₃),

b1 and b2 are each independently an integer selected from 0 to 4,

c1 is an integer selected from 1 to 4,

c2 is an integer selected from 0 to 4,

at least one selected from substituents of the substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₂₁)(Q₂₂)(Q₂₃),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, and Q₂₁ to Q₂₃ are each independentlyselected from a hydrogen, a deuterium, a C₁-C₆₀ alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group,

in *-(L₁)_(a1)-*′, * and *′ are each a binding site to a neighboringatom.

According to another aspect of an exemplary embodiment, an organiclight-emitting device includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer includes an emission layer and atleast one condensed cyclic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawing in which:

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the figures, to explain aspects. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

According to one or more exemplary embodiments, a condensed cycliccompound represented by Formula 1 is provided:

In Formula 1, X₁ may be N or C(R₁), X₂ may be N or C(R₂), X₃ may be N orC(R₃), X₄ may be N or C(R₄), X₅ may be N or C(R₅), X₆ may be N or C(R₆),X₇ may be N or C(R₇), X₁₁ may be N or C(R₁₁), X₁₂ may be N or C(R₁₂),X₁₃ may be N or C(R₁₃), X₁₄ may be N or C(R₁₄), X₁₅ may be N, C(R₁₅), ora carbon atom connected to *-(L₁)_(a1)-*′, X₁₆ may be N, C(R₁₆), or acarbon atom connected to *-(L₁)_(a1)-*′, X₁₇ may be N, C(R₁₇), or acarbon atom connected to *-(L₁)_(a1)-*′, and X₁₈ may be N, C(R₁₈), or acarbon atom connected to *-(L₁)_(a1)-*′, wherein one of X₁₅ to X₁₈ maybe connected to *-(L₁)_(a1)-*′.

For example, in Formula 1, X₁ may be C(R₁), X₂ may be C(R₂), X₃ may beC(R₃), X₄ may be C(R₄), X₅ may be C(R₅), X₆ may be C(R₆), X₇ may beC(R₇), X₁₁ may be C(R₁₁), X₁₂ may be C(R₁₂), X₁₃ may be C(R₁₃), X₁₄ maybe C(R₁₄), X₁₅ may be C(R₁₅) or a carbon atom connected to*-(L₁)_(a1)-*′, X₁₆ may be C(R₁₆) or a carbon atom connected to*-(L₁)_(a1)-*′, X₁₇ may be C(R₁₇) or a carbon atom connected to*-(L₁)_(a1)-*′, and X₁₈ may be C(R₁₈) or a carbon atom connected to*-(L₁)_(a1)-*′, wherein one of X₁₅ to X₁₈ may be connected to*-(L₁)_(a1)-*′.

In Formula 1, ring A₁ and ring A₂ may be each independently selectedfrom a C₅-C₆₀ carbocyclic group and a C₃-C₆₀ heterocyclic group thatincludes at least one heteroatom selected from O, S, and Si. When ringA₁ and ring A₂ are each a C₃-C₆₀ heterocyclic group, the C₃-C₆₀heterocyclic group includes at least one heteroatom selected from O, S,and Si as a ring-forming atom. That is, for example, ring A₁ and ring A₂may not be a C₃-C₆₀ heterocyclic group that includes N as a ring-formingatom. For example, ring A₁ and ring A₂ may not be a pyridine, apyrimidine, a triazine, or a carbazole.

For example, in Formula 1, ring A₁ and ring A₂ may be each independentlyselected from a cyclopentyl group, a cyclohexyl group, a cyclopentenylgroup, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthenyl group, afluorenyl group, a spirobifluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a furanyl group, a thiophenyl group, a benzofuranylgroup, a benzothiophenyl group, a dibenzofuranyl group, and adibenzothiophenyl group.

According to an embodiment, in Formula 1, ring A₁ and ring A₂ may beeach independently selected from a phenyl group, a dibenzofuranyl group,and a dibenzothiophenyl group, but embodiments are not limited thereto.

In Formula 1, L₁ to L₃ may be each independently selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group, a triazinylene group, afluorenylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group, a triazinylene group, afluorenylene group, a dibenzofuranylene group, and adibenzothiophenylene group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃).

For example, in Formula 1, L₁ to L₃ may be each independently selectedfrom

a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group, a triazinylene group, afluorenylene group, a dibenzofuranylene group, and adibenzothiophenylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group, apyrazinylene group, a pyridazinylene group, a triazinylene group, afluorenylene group, a dibenzofuranylene group, and adibenzothiophenylene group, each substituted with at least one selectedfrom a deuterium, a cyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, and —Si(Q₁₁)(Q₁₂)(Q₁₃),

wherein Q₁₁ to Q₁₃ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinylgroup, a pyrimidinyl group, and a triazinyl group.

According to an embodiment, in Formula 1, L₁ to L₃ may be eachindependently selected from groups represented by Formulae 3-1 to 3-56:

In Formulae 3-1 to 3-56,

Y₁ may be selected from O, S, and C(Z₃)(Z₄),

Z₁ to Z₄ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, adibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃),

wherein Q₁₁ to Q₁₃ may be each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group,

d4 may be an integer selected from 0 to 4,

d3 may be an integer selected from 0 to 3,

d2 may be an integer selected from 0 to 2, and

* and *′ may be each independently a binding site to a neighboring atom.

In Formula 1, a1 denotes the number of groups L₁, and is an integerselected from 0 to 5. When a1 is 0, *-(L₁)_(a1)-*′ is a single bond, andwhen a1 is 2 or greater, two or more groups L₁ may be identical to ordifferent from each other. Descriptions of a2 and a3 may be the same asdefined for a1 in Formula 1.

In Formula 1, a1 to a3 may be each independently an integer selectedfrom 0 to 5.

For example, in Formula 1, a1 to a3 may be each independently 0, 1, or2, but embodiments are not limited thereto.

According to an embodiment, in Formula 1, a1 may be 0.

According to another embodiment, in Formula 1, when a1 is not 0, atleast one of groups L₁ may be selected from groups represented byFormulae 3-15 to 3-56.

In some embodiments, in Formula 1, when a1 is not 0, all of groups L₁may be each independently selected from groups represented by Formulae3-15 to 3-56.

In some embodiments, in Formula 1,

L₁ may be selected from groups represented by Formulae 3-15, 3-28, 3-41,and 3-51,

L₂ and L₃ may be each independently selected from groups represented byFormulae 3-1, 3-15, 3-28, 3-41, and 3-51, and

a1 to a3 may be each independently 0, 1, or 2,

but embodiments are not limited thereto.

In Formula 1, a group represented by *-(L₁)_(a1)-*′ may be selected fromgroups represented by Formulae 3-41 to 3-56.

In some embodiments, in Formula 1, a group represented by *-(L₁)_(a1)-*′may be selected from groups represented by Formulae 4-1 to 4-39:

In Formulae 4-1 to 4-39, X₂₁ may be N or C(Z₂₁), X₂₂ may be N or C(Z₂₂),X₂₃ may be N or C(Z₂₃), X₂₄ may be N or C(Z₂₄), X₃₁ may be N or C(Z₃₁),X₃₂ may be N or C(Z₃₂), X₃₃ may be N or C(Z₃₃), X₃₄ may be N or C(Z₃₄),X₄₁ may be N or C(Z₄₁), X₄₂ may be N or C(Z₄₂), X₄₃ may be N or C(Z₄₃),and X₄₄ may be N or C(Z₄₄), provided that each of X₂₁ to X₂₄ are notsimultaneously N, provided that each of X₃₁ to X₃₄ are notsimultaneously N, and provided that each of X₄₁ to X₄₄ are notsimultaneously N,

Z₂₁ to Z₂₄, Z₃₁ to Z₃₄, and Z₄₁ to Z₄₄ may be each independentlyselected from a hydrogen, a deuterium, a cyano group, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, adibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃),

wherein Q₁₁ to Q₁₃ may be each independently a hydrogen, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, anda dibenzothiophenyl group, and

* and *′ may be each independently a binding site to a neighboring atom.

According to an embodiment, none, one, two, or three atoms among allring-forming atoms in each of Formulae 4-1 to 4-39 may be nitrogen.

According to another embodiment, none, one, or two atoms among allring-forming atoms in each of Formulae 4-1 to 4-39 may be nitrogen.

In some embodiments, none or one atom among all ring-forming atoms ineach of Formulae 4-1 to 4-39 may be nitrogen.

In some embodiments, in each of Formulae 4-1 to 4-39, X₂₁ may be C(Z₂₁),X₂₂ may be C(Z₂₂), X₂₃ may be C(Z₂₃), X₂₄ may be C(Z₂₄), X₃₁ may beC(Z₃₁), X₃₂ may be C(Z₃₂), X₃₃ may be C(Z₃₃), X₃₄ may be C(Z₃₄), X₄₁ maybe C(Z₄₁), X₄₂ may be C(Z₄₂), X₄₃ may be C(Z₄₃), and X₄₄ may be C(Z₄₄)(that is, none of the ring-forming atoms in each of Formulae 4-1 to 4-30may be nitrogen).

In Formula 1, R₁ to R₇, R₁₁ to R₁₈, and R₃₁ and R₃₂ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group (—CN), a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₁)(Q₂)(Q₃).

For example, in Formula 1, R₁ to R₇, R₁₁ to R₁₈, and R₃₁ and R₃₂ may beeach independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, anda triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthenyl group, afluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an isoindolyl group, an indolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, afuranyl group, a benzofuranyl group, a thiophenyl group, abenzothiophenyl group, a thiazolyl group, an isothiazolyl group, abenzothiazolyl group, an isoxazolyl group, an oxazolyl group, a thazolylgroup, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinylgroup, and an imidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthenyl group, afluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an isoindolyl group, an indolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalmyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, afuranyl group, a benzofuranyl group, a thiophenyl group, abenzothiophenyl group, a thiazolyl group, an isothiazolyl group, abenzothiazolyl group, an isoxazolyl group, an oxazolyl group, atriazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, animidazopyrimidinyl group, and an imidazopyridinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an anthracenyl group, a pyrenyl group, aphenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a phthalazinyl group, aquinoxalinyl group, a cinnolinyl group, a quinazolinyl group, and—Si(Q₂₁)(Q₂₂)(Q₂₃); and

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁ to Q₃ and Q₂₁ to Q₂₃ may be each independently selected froma hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenylgroup, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group a phthalazinyl group, a quinoxalinylgroup, a cinnolinyl group, and a quinazolinyl group.

According to an embodiment, in Formula 1, R₁ to R₇, R₁₁ to R₁₈, and R₃₁and R₃₂ may be each independently

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, afluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, afluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, and —Si(Q₂₁)(Q₂₂)(Q₂₃); and

—Si(Q₁)(Q₂)(Q₃),

Q₁ to Q₃ and Q₂₁ to Q₂₃ may be each independently selected from ahydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group.

According to another embodiment, in Formula 1, R₁ to R₇, R₁₁ to R₁₈, andR₃₁ and R₃₂ may be each independently selected from a hydrogen, adeuterium, —F, a cyano group, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxygroup;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, and a cyano group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, a cyanogroup, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₂₁)(Q₂₂)(Q₂₃);and

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁ to Q₃ and Q₂₁ to Q₂₃ may be each independently selected froma hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group,a pyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group.

According to an embodiment, in Formula 1, at least one of X₃, X₆, X₁₃,and X₁₆ may be C(CN).

In Formula 1, b1 may denote the number of R₃₁ which may be an integerselected from 0 to 4. When b1 is 2 or greater, two or more R₃₁ may beidentical to or different from each other. In Formula 1, b2 may denotethe number of R₃₂ which may be an integer selected from 0 to 4. When b2is 2 or greater, two or more R₃₂ may be identical to or different fromeach other.

In Formula 1, b1 and b2 may be each independently an integer selectedfrom 0 to 4. For example, in Formula 1, b1 and b2 may be eachindependently 0, 1, or 2.

In Formula 1, c1 may be an integer selected from 1 to 4. That is, ringA₁ may essentially include at least one cyano group. For example, inFormula 1, c1 may be 1 or 2.

In Formula 1, c2 may be an integer selected from 0 to 4. For example, inFormula 1, c2 may be 0 or 1.

According to an embodiment, in Formula 1, a group represented by

may be selected from groups represented by Formulae 5-1 to 5-60, and agroup represented by

may be selected from groups represented by Formulae 5-1 to 5-69:

In Formulae 5-1 to 5-69, * may denote a binding site to a neighboringatom.

According to an embodiment, in Formula 1, a group represented by

may be selected from groups represented by Formulae 5-1 to 5-3, 5-31,5-39, 5-47, and 5-55, and a group represented by

may be selected from groups represented by Formulae 5-1 to 5-3, 5-31,5-39, 5-47, 5-55, 5-61, 5-63, 5-65, 5-67, and 5-69, but embodiments arenot limited thereto.

A condensed cyclic compound represented by Formula 1 may be representedby one of Formulae 1A to 1D:

In Formulae 1A to 1D, ring A₁, ring A₂, L₁ to L₃, a1 to a3, R₁ to R₇,R₁₁ to R₁₈, R₃₁, R₃₂, b1, b2, c1, and c2 may be understood by referringto the description provided herein.

For example, in Formulae 1A to 1D, ring A₁ and ring A₂ may be eachindependently selected from a phenyl group, a dibenzofuranyl group, anda dibenzothiophenyl group,

L₁ may be selected from groups represented by Formulae 3-15, 3-28, 3-41,and 3-51,

L₂ and L₃ may be each independently selected from groups represented byFormulae 3-1, 3-15, 3-28, 3-41, and 3-51,

a1 to a3 may be each independently selected from 0, 1, and 2,

R₁ to R₇, R₁₁ to R₁₈, R₃₁, and R₃₂ may be each independently selectedfrom a hydrogen, a deuterium, —F, a cyano group, a C₁-C₁₀ alkyl group,and a C₁-C₁₀ alkoxy group;

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, and a cyano group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, a cyanogroup, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₂₁)(Q₂₂)(Q₂₃);and

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁ to Q₃ and Q₂₁ to Q₂₃ may be each independently selected froma hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group,a pyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group,

b1 and b2 may be each independently 0 or 1,

c1 may be 1 or 2, and

c2 may be 0, 1, or 2.

According to another embodiment, in Formulae 1A to 1D, a grouprepresented by

may be selected from groups represented by Formulae 5-1 to 5-3, 5-31,5-39, 5-47, and 5-55, and a group represented by

may be selected from groups represented by Formulae 5-1 to 5-3, 5-31,5-39, 5-47, 5-55, 5-61, 5-63, 5-65, 5-67, and 5-69, but embodiments arenot limited thereto.

In some embodiments, in Formulae 1A to 1D, at least one of R₃, R₆, R₁₃,and R₁₆ may be a cyano group.

In some embodiments, the number of cyano groups in Formula 1 may be 1,2, 3, or 4.

A compound represented by Formula 1 may be one of Compounds 1 to 271,but embodiments are not limited thereto:

In Formula 1, “ring B” is bonded to the first carbon of “ring A” via*-(L₁)_(a1)-*′ (see Formula 1′).

In this regard, the condensed cyclic compound represented by Formula 1may have a high triplet (T₁) energy level. For example, although notlimited to a particular theory, the condensed cyclic compoundrepresented by Formula 1 may have a T₁ energy level that is at leastabout 0.05 electron volts (eV) higher than that of a virtual compoundhaving the same structure as the condensed cyclic compound representedby Formula 1 except that “ring B” bonded to the third carbon of “ring A”via *-(L₁)_(a1)-*′.

Also, in Formula 1, c1 may be an integer selected from 1 to 4. That is,in Formula 1, ring A₁ essentially includes at least one cyano group.Thus, in the condensed cyclic compound represented by Formula 1, ring A₁essentially including at least one cyano group is connected with “N” of“ring B” via *-(L₂)_(a2)-*′ and has a structure in which one of X₁₅ toX₁₈ of “ring B” is essentially connected to the first carbon of “ring A”via *-(L₁)_(a1)-*′.

In this regard, the condensed cyclic compound represented by Formula 1may have a high T₁ energy level, where the HOMO and LUMO energy levelsof the condensed cyclic compound represented by Formula 1 may besuitable for an organic light-emitting device material, such as, aphosphorescent host material. For example, the condensed cyclic compoundrepresented by Formula 1 having c1, which is an integer selected from 1to 4, may have an energy band gap and a singlet (S₁) energy level thatare suitable for a material of a single host for an organiclight-emitting device. For example, although not limited to a particulartheory, a virtual compound having the same structure as the condensedcyclic compound represented by Formula 1 except that c1 is 0 may have anenergy band gap that is broader than that of the condensed cycliccompound represented by Formula 1 and a relatively high S₁ energy level,and thus the virtual compound may be improper for using as an organiclight-emitting device material, such as a single host material and mayhave a relatively low optical stability.

Also, a difference between S₁ (singlet) energy level and T₁ (triplet)energy level of the condensed cyclic compound represented by Formula 1may be relatively small. In this regard, the condensed cyclic compoundrepresented by Formula 1 may be used as a thermally activated delayedfluorescence (TADF) emitter.

For example, the results of HOMO, LUMO, T₁, and S₁ energy levels ofCompounds 1 to 8, 11 to 13, 16, 31 and 136 and Compounds B and Csimulated and measured by using a density functional theory (“DFT”)method of Gaussian program (structurally optimized at a level of B3LYP,6-31 G(d,p)) are shown in Table 1.

TABLE 1 Compound No. HOMO (eV) LUMO (eV) T₁ (eV) S₁ (eV)  1 −5.4 −1.483.09 3.28   2 −5.524 −1.513 3.104 3.433  3 −5.501 −1.531 3.08 3.395  4−5.613 −1.626 3.082 3.317  5 −5.662 −1.76 3.087 3.203  6 −5.688 −1.6973.074 3.311  7 −5.769 −1.72 3.077 3.432  8 −5.786 −1.715 3.075 3.439  11−5.641 −1.766 3.067 3.275  12 −5.71 −1.792 3.075 3.386  13 −5.7 −1.8133.07 3.346  16 −5.181 −1.754 3.061 3.122  31 −5.253 −1.679 3.034 3.195136 −5.421 −1.516 3.054 3.347 Compound B −5.19 −1.65 2.8 3.212 CompoundC −5.34 −1.43 2.9 3.444

A method of synthesizing the condensed cyclic compound represented byFormula 1 may be understood by one of ordinary skill in the art byreferring to Synthesis Examples described below.

Therefore, the condensed cyclic compound represented by Formula 1 may besuitable for use as an organic layer of an organic light-emitting deviceor, for example, as a host or an emitter (e.g., a TADF emitter) of anemission layer in the organic layer. According to another aspect of anembodiment, an organic light-emitting device includes:

a first electrode;

a second electrode; and

an organic layer that is disposed between the first electrode and thesecond electrode, wherein the organic layer includes an emission layerand at least one condensed cyclic compounds represented by Formula 1.

While not wishing to be bound by a theory, it is understood that whenthe organic light-emitting device includes the organic layer includingthe condensed cyclic compound represented by Formula 1, the organiclight-emitting device may have a low driving voltage, high efficiency,high luminance, high quantum efficiency, and long lifespan.

The condensed cyclic compound represented by Formula 1 may be includedin between a pair of electrodes of the organic light-emitting device. Insome embodiments, the condensed cyclic compound may be included in atleast one selected from the emission layer, a hole transport region (forexample, including at least one selected from a hole injection layer, ahole transport layer, and an electron blocking layer) disposed betweenthe first electrode and the emission layer, and an electron transportregion (for example, including at least one selected from a holeblocking layer, an electron transport layer, and an electron injectionlayer) disposed between the emission layer and the second electrode.

In some embodiments, the condensed cyclic compound represented byFormula 1 may be included in the emission layer. Here, the condensedcyclic compound included in the emission layer may be a host, and theemission layer may further include a dopant (a fluorescent dopant or aphosphorescent dopant), wherein a weight of the condensed cycliccompound is greater than a weight of the dopant. The emission layer maybe a green emission layer or a blue emission layer that emits greenlight or blue light. According to an embodiment, the condensed cycliccompound represented by Formula 1 may be included in the emission layer,the emission layer may further include a phosphorescent dopant, and theemission layer may emit blue light.

In some embodiments, the condensed cyclic compound represented byFormula 1 may be included in the emission layer, and the condensedcyclic compound may be a TADF emitter. Here, the emission layer mayinclude the condensed cyclic compound represented by Formula 1 only ormay further include a host and/or a dopant in addition to the condensedcyclic compound represented by Formula 1.

As used herein, the expression “(an organic layer) includes at least onecondensed cyclic compound” may include an embodiment in which (anorganic layer) includes one condensed cyclic compounds represented byFormula 1 and an embodiment in which (an organic layer) includes two ormore different condensed cyclic compounds represented by Formula 1.

For example, the organic layer may include only Compound 1 as thecondensed cyclic compound. In this regard, Compound 1 may be included inthe emission layer of the organic light-emitting device. In someembodiments, the organic layer may include Compound 1 and Compound 2 asthe condensed cyclic compounds. In this regard, Compound 1 and Compound2 may be included in the same layer (for example, both Compound 1 andCompound 2 may be included in the emission layer) or in differentlayers, respectively.

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode. Alternatively, the first electrode may bea cathode, which is an electron injection electrode, and the secondelectrode may be an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, the second electrodemay be a cathode, and the organic layer may include:

i) a hole transport region disposed between the first electrode and theemission layer, wherein the hole transport region includes at least oneselected from a hole injection layer, a hole transport layer, and anelectron blocking layer; and

ii) an electron transport region disposed between the emission layer andthe second electrode, wherein the electron transport region includes atleast one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer.

As used herein, the term “organic layer” refers to a single and/or aplurality of layers disposed between the first electrode and the secondelectrode in an organic light-emitting device. The “organic layer” mayinclude not only organic compounds but also organometallic complexesincluding metals.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, a structure and a method ofmanufacturing an organic light-emitting device, according to anembodiment, will be described with reference to FIG. 1. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially layered in thestated order.

A substrate may be additionally disposed under the first electrode 11 oron the second electrode 19. The substrate may be a conventionalsubstrate that is used in an organic light-emitting device, such as aglass substrate or a transparent plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellency.

The first electrode 11 may be formed by depositing or sputtering a firstelectrode material on the substrate. The first electrode 11 may be ananode. The first electrode material may be selected from materials witha high work function to facilitate hole injection. The first electrode11 may be a reflective electrode, a semi-transmissive electrode, or atransmissive electrode. The first electrode material may be selectedfrom indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂),and zinc oxide (ZnO). In some embodiments, a metal such as magnesium(Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as thefirst electrode material.

The first electrode 11 may have a single layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 11 may have a triple-layer structure of ITO/Ag/ITO, butembodiments are not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, a hole transport layer, an electron blocking layer, anda buffer layer.

The hole transport region may only include a hole injection layer or ahole transport layer. Alternatively, the hole transport region mayinclude a structure in which a hole injection layer/a hole transportlayer or a hole injection layer/a hole transport layer/an electronblocking layer are sequentially layered on the first electrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using variousmethods such as vacuum deposition, spin coating, casting, andLangmuir-Blodgett (LB) method.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100° C. toabout 500° C., a vacuum pressure of about 10⁻⁸ torr to about 10⁻³ torr,and a deposition rate of about 0.01 Angstroms per second (Å/sec) toabout 100 Å/sec. However, the deposition conditions are not limitedthereto.

When the hole injection layer is formed by spin coating, the coatingconditions may vary according to a material used to form the holeinjection layer and the structure and thermal characteristics of thehole injection layer. For example, a coating rate may be from about2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperatureat which a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

The conditions for forming a hole transport layer and an electronblocking layer may be inferred based on the conditions for forming thehole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/D BSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (Pani/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

In Formula 201, Ar₁₀₁ and Ar₁₀₂ may be each independently selected froma phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthenylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and a phenylene group, a pentalenylenegroup, an indenylene group, a naphthylene group, an azulenylene group, aheptalenylene group, an acenaphthenylene group, a fluorenylene group, aphenalenylene group, a phenanthrenylene group, an anthracenylene group,a fluoranthenylene group, a triphenylenylene group, a pyrenylene group,a chrysenylenylene group, a naphthacenylene group, a picenylene group, aperylenylene group, and a pentacenylene group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.

In Formula 201, xa and xb may be each independently an integer selectedfrom 0 to 5 or may be 0, 1, or 2. For example, xa may be 1, and xb maybe 0, but embodiments are not limited thereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄may be each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group(e.g., a methyl group, an ethyl group, a propyl group, a butyl group,pentyl group, or a hexyl group), and a C₁-C₁₀ alkoxy group (e.g., amethoxy group, an ethoxy group, a propoxy group, a butoxy group, or apentoxy group);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but embodiments are notlimited thereto.

In Formula 201, R₁₀₉ may be selected from a phenyl group, a naphthylgroup, an anthracenyl group, and a pyridinyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, and a pyridinyl group.

According to an embodiment, a compound represented by Formula 201 may berepresented by Formula 201A, but embodiments are not limited thereto:

In Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20, butembodiments are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, the thickness of the hole injection layermay be in a range of about 100 Å to about 10,000 Å, and for example,about 100 Å to about 1,000 Å, and the thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, and for example,about 100 Å to about 1,500 Å. While not wishing to be bound by a theory,it is understood that when the thicknesses of the hole transport region,the hole injection layer, and the hole transport layer are within theseranges, hole transporting characteristics may be satisfactory without asubstantial increase in driving voltage.

The hole transport region may further include, in addition to thementioned materials above, a charge-generating material to improveconductive properties. The charge-generating material may behomogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. Non-limiting examples of the p-dopant are a quinone derivative,such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyanogroup-containing compound, such as Compound HT-D1 or HP-1, butembodiments are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer toimprove the efficiency of an organic light-emitting device.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied toform the hole injection layer although the deposition or coatingconditions may vary depending on the material that is used to form theemission layer.

The hole transport region may further include an electron blockinglayer. The electron blocking layer may include, for example, mCP, butembodiments are not limited thereto.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer.Alternatively, the emission layer may have a structure in which the redemission layer, the green emission layer, and/or the blue emission layerare layered to emit white light or other various embodiments arepossible.

The emission layer may include the condensed cyclic compound representedby Formula 1. The emission layer may further include a dopant. Thedopant may include at least one selected from a fluorescent dopant and aphosphorescent dopant.

In some embodiments, the emission layer may include the condensed cycliccompound represented by Formula 1 only, and the condensed cycliccompound may be a TADF emitter.

In some embodiments, the emission layer may include the condensed cycliccompound represented by Formula 1, the condensed cyclic compound may bea TADF emitter, and the emission layer may further include any host notbeing the condensed cyclic compound represented by Formula 1.

For example, a host in the emission layer may include the condensedcyclic compound represented by Formula 1.

The dopant in the emission layer may include a fluorescent dopant whichemits light according to a fluorescent emission mechanism or aphosphorescent dopant which emits light according to a phosphorescentemission mechanism.

According to an embodiment, the dopant in the emission layer may be aphosphorescent dopant, and the phosphorescent dopant may include anorganometallic compound represented by Formula 81:

wherein, in Formula 81,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm),

Y₁ to Y₄ may be each independently carbon (C) or nitrogen (N),

Y₁ and Y₂ are linked via a single bond or a double bond, and Y₃ and Y₄are linked via a single bond or a double bond,

CY₁ and CY₂ may be each independently selected from a benzene ring, anaphthalene ring, a fluorene ring, a spiro-fluorene ring, an indenering, a pyrrole ring, a thiophene ring, a furan ring, an imidazole ring,a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring,an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring,a pyridazine ring, a quinoline ring, an isoquinoline ring, abenzoquinoline ring, a quinoxaline ring, a quinazoline ring, a carbazolering, a benzoimidazole ring, a benzofuran ring, a benzothiophene ring,an isobenzothiophene ring, a benzoxazole ring, an isobenzoxazole ring, atriazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, adibenzofuran ring, or a dibenzothiophene ring, and CY₁ and CY₂ areoptionally further linked to each other through an organic linkinggroup,

R₈₁ and R₈₂ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇),

a81 and a82 may be each independently an integer selected from 1 to 5,

n81 may be an integer selected from 0 to 4,

n82 may be 1, 2, or 3, and

L₈₁ may be a monovalent organic ligand, a divalent organic ligand, or atrivalent organic ligand, and

Q₁ to Q₇ may have the same definitions as Q₁ to Q₃ in —Si(Q₁)(Q₂)(Q₃) inFormula

R₈₁ and R₈₂ may be understood by referring to the description providedherein in connection with R₁₁.

The phosphorescent dopant may include at least one selected fromCompounds PD1 to PD78, and FIr₆, but embodiments are not limitedthereto:

In some embodiments, the phosphorescent dopant may include PtOEP:

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 part to about 20 parts by weightbased on 100 parts by weight of the host, but embodiments are notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by a theory, it is understood that when thethickness of the emission layer is within this range, light-emissioncharacteristics may be excellent without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer, but embodiments not limited thereto.

For example, the electron transport region may have a structure of ahole blocking layer/an electron transport layer/an electron injectionlayer or an electron transport layer/an electron injection layer, butembodiments are not limited thereto. The electron transport layer mayhave a single layer structure or a multi-layer structure including twoor more different materials.

The conditions for forming a hole blocking layer, an electron transportlayer, and an electron injection layer may be inferred based on theconditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one selected fromBCP and Bphen, but embodiments are not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by a theory, it is understood that when thethickness of the hole blocking layer is within these ranges, the holeblocking layer may have improved hole blocking ability without asubstantial increase in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, BPhen, Alq₃, BAlq, TAZ, and NTAZ.

In some embodiments, the electron transport layer may include at leastone selected from Compounds ET1, ET2, and ET3, but embodiments are notlimited thereto.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by a theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

The electron transport layer may further include a metal-containingmaterial in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layerthat allows electrons to be easily provided from a second electrode 19.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by a theory, it is understood that when thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A second electrode material may beselected from a metal, an alloy, an electrically conductive compound,and a combination thereof, which have a relatively low work function.For example, lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be formed as second electrode material. Tomanufacture a top emission type light-emitting device, a transmissiveelectrode formed using ITO or IZO may be used as the second electrode19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but embodiments are not limited thereto.

A C₁-C₆₀ alkyl group as used herein refers to a linear or branchedaliphatic saturated hydrocarbon monovalent group having 1 to 60 carbonatoms. Detailed examples thereof are a methyl group, an ethyl group, apropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup as used herein refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group as used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group as used herein refers to a hydrocarbon groupformed by placing at least one carbon-carbon double bond in the middleor at the terminal of the C₂-C₆₀ alkyl group. Detailed examples thereofare an ethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group as used herein refers to a hydrocarbon groupformed by placing at least one carbon-carbon triple bond in the middleor at the terminal of the C₂-C₆₀ alkyl group. Detailed examples thereofare an ethynyl group, and a propynyl group. A C₂-C₆₀ alkynylene group asused herein refers to a divalent group having the same structure as theC₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalentmonocyclic saturated hydrocarbon group including 3 to 10 carbon atoms.Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as a C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentsaturated monocyclic group including at least one hetero atom selectedfrom N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms.Detailed examples thereof are a tetrahydrofuranyl group and atetrahydrothiophenyl group. A C₁-C₁₀ heterocycloalkylene group as usedherein refers to a divalent group having the same structure as a C₁-C₁₀heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof, and which is not aromatic. Detailed examplesthereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group as used hereinrefers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group including at least one heteroatom selected from N, O,P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at leastone double bond in its ring. Detailed examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as aC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving a heterocyclic aromatic system that has at least one hetero atomselected from N, O, P, Si and S as a ring-forming atom, and 1 to 60carbon atoms. A C₁-C₆₀ heteroarylene group as used herein refers to adivalent group having a heterocyclic aromatic system that has at leastone hetero atom selected from N, O, P, Si and S as a ring-forming atom,and 1 to 60 carbon atoms. Examples of the C₁-C₆₀ heteroaryl group are apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylenegroup each include two or more rings, the rings may be fused to eachother.

A C₆-C₆₀ aryloxy group as used herein indicates —OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as used hereinindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group as used hereinrefers to a monovalent group that has two or more rings condensed toeach other, only carbon atoms (for example, the number of carbon atomsmay be in a range of 8 to 60) as ring-forming atoms, wherein themolecular structure as a whole is non-aromatic in the entire molecularstructure. Detailed example of the non-aromatic condensed polycyclicgroup includes a fluorenyl group. A divalent non-aromatic condensedpolycyclic group as used herein refers to a divalent group having thesame structure as the monovalent non-aromatic condensed polycyclicgroup.

A monovalent non-aromatic condensed hetero-polycyclic group as usedherein refers to a monovalent group that has a plurality of ringscondensed with each other, has a hetero atom selected from N, O, P, Siand S, other than carbon atoms (for example, the number of carbon atomsmay be in a range of 1 to 60), as ring-forming atoms, wherein themolecular structure as a whole is non-aromatic in the entire molecularstructure. The monovalent non-aromatic condensed heteropolycyclic groupincludes a carbazolyl group. A divalent non-aromatic condensedhetero-polycyclic group as used herein refers to a divalent group havingthe same structure as the monovalent non-aromatic condensedhetero-polycyclic group.

At least one substituent of the substituted C₃-C₁₀ cycloalkylene group,substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted a divalent non-aromatic condensed polycyclic group,substituted a divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group (where, a carbazolyl groupis excepted from the monovalent non-aromatic condensed heteropolycyclicgroup) and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may be eachindependently selected from a hydrogen, a C₁-C₆₀ alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group (where, a carbazolyl group is excepted from themonovalent non-aromatic condensed heteropolycyclic group).

When a group containing a specified number of carbon atoms issubstituted with any of the substituents listed above, the number ofcarbon atoms in the resulting “substituted” group may be the number ofatoms contained in the original (base) group plus the number of carbonatoms (if any) contained in the substituent. For example, the“substituted C₁-C₃₀ alkyl” may refer to a C₁-C₃₀ alkyl group substitutedwith C₆₋₆₀ aryl group, in which the total number of carbon atoms may beC₇-C₉₀.

The “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group”.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLE Synthesis Example 1 Synthesis of Compound 16

Synthesis of Intermediate 16-1

21.838 grams (g) (74.49 millimoles (mmol)) of2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, 20 g(61.07 mmol) of 1-bromo-9-phenyl-9H-carbazole, 14.346 g (12.41 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 27.863 g (496.59mmol) of potassium hydroxide were added to 200 milliliters (mL) of THFand 100 mL of distilled water in a round-bottomed flask, and the mixturewas heated under reflux for 12 hours. Once the reaction was completed,the reaction product was cooled to room temperature, and THF wasseparated from distilled water. Next, the THF layer separated therefromwas added dropwise to 600 mL of methanol and crystallized. The solid wasfiltered and washed with water and methanol. The resultant solid wasdried in a vacuum oven to obtain Intermediate 16-1 (21 g, the yield of85%).

Synthesis of Compound 16

12.3 g (30.11 mmol) of Intermediate 16-1, 3.27 mL (30.11 mmol) of2-fluorobenzonitrile, and 1.566 g (39.14 mmol) of sodium hydride wereadded to 200 mL of DMF in a round-bottomed flask, and the mixture washeated under reflux for 12 hours. Once the reaction was completed, thereaction product was cooled to room temperature, and added dropwise to600 mL of methanol and crystallized. The solid was filtered, and washedwith water and methanol. The resultant solid was dried in a vacuum ovento obtain Compound 16 (10.74 g, the yield of 70%).

1H NMR (400 MHz, CDCl₃): δ 8.23 (d, 1H), 8.20 (d, 1H), 7.97 (d, 1H),7.92 (d, 1H), 7.84 (t, 1H), 7.71 (s, 1H), 7.64 (t, 1H), 7.53 (d, 1H),7.47 (d, 1H), 7.43 (m, 4H), 7.32 (m, 4H), 7.16 (t, 3H), 6.82 (d, 2H),6.74 (t, 1H). MS (m/z, [M]+): 509.06

Synthesis Example 2 Synthesis of Compound 31

Synthesis of Intermediate 31-1

16.378 g (55.87 mmol) of3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, 15 g(46.55 mmol) of 1-bromo-9-phenyl-9H-carbazole, 10.759 g (9.31 mmol) oftetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄], and 20.898 g (372.44mmol) of potassium hydroxide were added to 200 mL THF and 100 mL ofdistilled water in a round-bottomed flask, and the mixture was heatedunder refluxed for 12 hours. Once the reaction was completed, thetemperature was decreased to room temperature, and THF was separatedfrom distilled water. The THF separated therefrom was added dropwise to600 mL of methanol and crystallized. The solid was filtered, and washedwith water and methanol. The resultant solid obtained therefrom wasdried in a vacuum oven to obtain Intermediate 31-1 (13 g, the yield of68%).

Synthesis of Compound 31

10 g (24.48 mmol) of Intermediate 31-1, 2.66 mL (24.48 mmol) of2-fluorobenzonitrile, and 1.27 g (31.82 mmol) of sodium hydride wereadded to 150 mL of DMF in a round-bottomed flask, and the mixture washeated under reflux for 12 hours. Once the reaction was completed, thereaction product was cooled to room temperature, and added dropwise to600 mL of methanol and crystallized. The solid was filtered, and washedwith water and methanol. The resultant solid was dried in a vacuum ovento obtain Compound 31 (8.98 g, the yield of 72%).

1H NMR (400 MHz, CDCl₃): δ 8.20 (d, 1H), 8.17 (d, 1H), 8.07 (d, 1H),7.79 (t, 1H), 7.72 (d, 1H), 7.59 (m, 3H), 7.40 (m, 7H), 7.22 (t, 2H),7.03 (d, 2H), 6.90 (t, 4H). MS (m/z, [M]+): 509.06

Evaluation Example 1 Evaluation on HOMO and LUMO Energy Levels

HOMO and LUMO energy levels of Compounds 16 and 31 were evaluatedaccording to the method indicated in Table 2, and results thereof areshown in Table 3.

TABLE 2 HOMO energy level A potential (V)-current (A) graph of eachevaluation method compound was obtained by using cyclic voltammetry (CV)(electrolyte: 0.1 molar (M) Bu₄NClO₄/solvent: CH₂Cl₂/electrode: 3electrode system (working electrode: GC, reference electrode: Ag/AgCl,auxiliary electrode: Pt)). From oxidation onset of the graph, a HOMOenergy level of the compound was calculated. LUMO energy level Eachcompound was diluted at a concentration of evaluation method 1 × 10⁻⁵Min CHCl₃, and an UV absorption spectrum thereof was measured at roomtemperature by using Shimadzu UV-350 Spectrometer. A LUMO energy levelthereof was calculated by using an optical band gap (E_(g)) from an edgeof the absorption spectrum and a HOMO energy level.

TABLE 3 HOMO (eV) LUMO (eV) Compound No. (found) (found) 16 −5.63 −2.1931 −5.61 −2.15

From Table 3, it is confirmed that Compounds 16 and 31 have electriccharacteristics that are suitable for use as a material for forming anorganic light-emitting device.

Evaluation Example 2 Thermal Characteristics Evaluation

Each of Compounds 16, 31, and A was subjected to thermal analysis (N₂atmosphere, temperature range: room temperature to 800° C. (10°C./min)-TGA, room temperature to 400° C.-DSC, Pan Type: Pt Pan indisposable Al Pan(TGA), disposable Al pan(DSC)) using thermogravimetricanalysis (TGA) and differential scanning calorimetry (DSC), and obtainedresults are shown in Table 4 below. Based on the data in Table 4, it wasconfirmed that Compounds 16 and 31 had excellent thermal stability thanthat of Compound A.

TABLE 4 Compound No. T_(g)(° C.) 16 115 31 114 Compound A  72

Example 1

A glass substrate with a 1,500 Angstrom (Å)-thick ITO (Indium tin oxide)electrode (first electrode, anode) formed thereon was washed withdistilled water and ultrasonic waves. When the washing with distilledwater was completed, sonification washing was performed using a solvent,such as isopropyl alcohol, acetone, or methanol. The resultant was driedand transferred to a plasma washer. The resultant substrate was washedwith oxygen plasma for 5 minutes and transferred to a vacuum depositor.

Compound HT3 and Compound HP-1 were co-deposited on the ITO electrode onthe glass substrate to form a hole injection layer having a thickness of100 Å, and Compound HT3 was deposited on the hole injection layer toform a hole transport layer having a thickness of 1,300 Å. mCP wasdeposited on the hole transport layer to form an electron blocking layerhaving a thickness of 150 Å, thereby completing the manufacture of ahole transport region.

Compound 16 (host) and FIr6 (dopant, 10 percent by weight (wt %)) wereco-deposited on the hole transport region to form an emission layerhaving a thickness of 300 Å.

BCP was vacuum deposited on the emission layer to form a hole blockinglayer having a thickness of 100 Å, Compound ET3 and Liq were vacuumdeposited on the hole blocking layer to form an electron transport layerhaving a thickness of 250 Å. Then, Liq was deposited on the electrontransport layer to form an electron injection layer having a thicknessof 5 Å, and Al second electrode (cathode) having a thickness of 1,000 Åwas formed on the electron injection layer, thereby completing themanufacture of an organic light-emitting device.

Example 2 and Comparative Example 1

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that the compounds shown in Table 4 were used, as ahost, instead of Compound 16 in the formation of the emission layer.

Evaluation Example 3 Evaluation on Characteristics of OrganicLight-Emitting Devices

The driving voltage, current density, efficiency, power efficiency,quantum efficiency, and lifespan of the organic light-emitting devicesof Examples 1 and 2 and Comparative Example 1 were measured by using acurrent-voltage meter (Keithley 2400) and a luminance meter (MinoltaCs-1000A), and results thereof are shown in Table 5. T₉₅ (at 500candelas per square meter (cd/m²)) in Table 5 indicates an amount oftime that lapsed when 100% of the initial luminance was decreased to95%.

TABLE 5 Power Quantum Driving voltage Efficiency Efficiency EfficiencyT₉₅ Host (V) (cd/A) (lm/W) (%) (hr) Example 1 Compound 16 5.03 35.1521.95 19.1 3.66 Example 2 Compound 31 5.12 39.25 24.16 19.5 2.24Comparative Compound A 6.85 15.27  7.03  8.9 0.54 Example 1

Referring to Table 5, it was confirmed that the organic light-emittingdevices of Examples 1 and 2 have a lower driving voltage, a higherefficiency, a higher power efficiency, a higher quantum luminescentefficiency, and a longer lifespan than the organic light-emitting deviceof Comparative Example 1.

As described above, according to the one or more of the aboveembodiments of the present inventive concept, a condensed cycliccompound has excellent electric characteristics and thermal stability,and thus an organic light-emitting device including the condensed cycliccompound may have a low driving voltage, high efficiency, high powerefficiency, high quantum luminescent efficiency, and long lifespancharacteristics.

It should be understood that exemplary embodiments described hereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the figures, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope of the presentdisclosure as defined by the following claims.

What is claimed is:
 1. A condensed cyclic compound represented byFormula 1:

wherein, in Formula 1, X₁ is N or C(R₁), X₂ is N or C(R₂), X₃ is N orC(R₃), X₄ is N or C(R₄), X₅ is N or C(R₅), X₆ is N or C(R₆), X₇ is N orC(R₇), X₁₁ is N or C(R₁₁), X₁₂ is N or C(R₁₂), X₁₃ is N or C(R₁₃), X₁₄is N or C(R₁₄), X₁₅ is N, C(R₁₅), or a carbon atom connected to*-(L₁)_(a1)-*′, X₁₆ is N, C(R₁₆), or a carbon atom connected to*-(L₁)_(a1)-*′, X₁₇ is N, C(R₁₇), or a carbon atom connected to*-(L₁)_(a1)-*′, and X₁₈ is N, C(R₁₈), or a carbon atom connected to*-(L₁)_(a1)-*′, wherein one of X₁₅ to X₁₈ is connected to*-(L₁)_(a1)-*′, ring A₁ and ring A₂ are each independently selected froma C₅-C₆₀ carbocyclic group and a C₃-C₆₀ heterocyclic group comprising atleast one heteroatom selected from O, S, and Si, L₁ to L₃ are eachindependently selected from a phenylene group, a pyridinylene group, apyrimidinylene group, a pyrazinylene group, a pyridazinylene group, atriazinylene group, a fluorenylene group, a dibenzofuranylene group, anda dibenzothiophenylene group; and a phenylene group, a pyridinylenegroup, a pyrimidinylene group, a pyrazinylene group, a pyridazinylenegroup, a triazinylene group, a fluorenylene group, a dibenzofuranylenegroup, and a dibenzothiophenylene group, each substituted with at leastone selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, and—Si(Q₁₁)(Q₁₂)(Q₁₃), a1 to a3 are each independently an integer selectedfrom 0 to 5, wherein when a1 is 2 or greater, two or more groups L₁ areidentical to or different from each other, when a2 is 2 or greater, twoor more groups L₂ are identical to or different from each other, andwhen a3 is 2 or greater, two or more groups L₃ are identical to ordifferent from each other, R₁ to R₇, R₁₁ to R₁₈, R₃₁, and R₃₂ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group (CN), a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₁)(Q₂)(Q₃), b1 and b2 areeach independently an integer selected from 0 to 4, c1 is an integerselected from 1 to 4, c2 is an integer selected from 0 to 4, at leastone selected from substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₁-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic condensed heteropolycyclic group isselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₂₁)(Q₂₂)(Q₂₃), wherein Q₁ toQ₃, Q₁₁ to Q₁₃, and Q₂₁ to Q₂₃ are each independently selected from ahydrogen, a deuterium, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group, in *-(L₁)_(a1)-*′, * and *′ are each a bindingsite to a neighboring atom.
 2. The condensed cyclic compound of claim 1,wherein ring A₁ and ring A₂ are each independently selected from acyclopentyl group, a cyclohexyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthenyl group, afluorenyl group, a spirobifluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a furanyl group, a thiophenyl group, a benzofuranylgroup, a benzothiophenyl group, a dibenzofuranyl group, and adibenzothiophenyl group.
 3. The condensed cyclic compound of claim 1,wherein ring A₁ and ring A₂ are each independently selected from aphenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. 4.The condensed cyclic compound of claim 1, wherein L₁ to L₃ are eachindependently selected from groups represented by Formulae 3-1 to 3-56:

wherein, in Formulae 3-1 to 3-56, Y₁ is selected from O, S, andC(Z₃)(Z₄), Z₁ to Z₄ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, adibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃), wherein Q₁₁ to Q₁₃ areeach independently selected from a hydrogen, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a fluorenyl group, a dibenzofuranyl group, and adibenzothiophenyl group, d4 is an integer selected from 0 to 4, d3 is aninteger selected from 0 to 3, d2 is an integer selected from 0 to 2,and * and *′ are each a binding site to a neighboring atom.
 5. Thecondensed cyclic compound of claim 4, wherein i) a1 is 0; or ii) when a1is not 0, at least one of groups L₁ is selected from groups representedby Formulae 3-15 to 3-56.
 6. The condensed cyclic compound of claim 4,wherein L₁ is selected from groups represented by Formulae 3-15, 3-28,3-41, and 3-51, L₂ and L₃ are each independently selected from groupsrepresented by Formulae 3-1, 3-15, 3-28, 3-41, and 3-51, and a1 to a3are each independently 0, 1, or
 2. 7. The condensed cyclic compound ofclaim 1, wherein a group represented by *-(L₁)_(a1)-*′ is selected fromgroups represented by Formulae 4-1 to 4-39:

wherein, in Formulae 4-1 to 4-39, X₂₁ is N or C(Z₂₁), X₂₂ is N orC(Z₂₂), X₂₃ is N or C(Z₂₃), X₂₄ is N or C(Z₂₄), X₃₁ is N or C(Z₃₁), X₃₂is N or C(Z₃₂), X₃₃ is N or C(Z₃₃), X₃₄ is N or C(Z₃₄), X₄₁ is N orC(Z₄₁), X₄₂ is N or C(Z₄₂), X₄₃ is N or C(Z₄₃), and X₄₄ is N or C(Z₄₄),provided that each of X₂₁ to X₂₄ is not simultaneously N, provided thateach of X₃₁ to X₃₄ is not simultaneously N, and provided that each ofX₄₁ to X₄₄ is not simultaneously N, Z₂₁ to Z₂₄, Z₃₁ to Z₃₄, and Z₄₁ toZ₄₄ are each independently selected from a hydrogen, a deuterium, acyano group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, and—Si(Q₁₁)(Q₁₂)(Q₁₃), wherein Q₁₁ to Q₁₃ are each independently ahydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group, and * and *′ areeach a binding site to a neighboring atom.
 8. The condensed cycliccompound of claim 1, wherein R₁ to R₇, R₁₁ to R₁₈, R₃₁, and R₃₂ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxygroup; a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, and aphosphoric acid group or a salt thereof; a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group; a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, and —Si(Q₂₁)(Q₂₂)(Q₂₃); and—Si(Q₁)(Q₂)(Q₃), wherein Q₁ to Q₃ and Q₂₁ to Q₂₃ are each independentlyselected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group.
 9. Thecondensed cyclic compound of claim 1, wherein R₁ to R₇, R₁₁ to R₁₈, andR₃₁ and R₃₂ are each independently selected from a hydrogen, adeuterium, —F, a cyano group, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxygroup; a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substitutedwith at least one selected from a deuterium, —F, and a cyano group; aphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group,a dibenzofuranyl group, and a dibenzothiophenyl group; a phenyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, a cyano group, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, and —Si(Q₂₁)(Q₂₂)(Q₂₃); and—Si(Q₁)(Q₂)(Q₃), Q₁ to Q₃ and Q₂₁ to Q₂₃ are each independently ahydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group.
 10. The condensedcyclic compound of claim 1, wherein at least one of X₃, X₆, X₁₃, and X₁₆is C(CN).
 11. The condensed cyclic compound of claim 1, wherein a grouprepresented by

is selected from groups represented by Formulae 5-1 to 5-60, and a grouprepresented by

is selected from groups represented by Formulae 5-1 to 5-69:

wherein, in Formulae 5-1 to 5-69, * is a binding site to a neighboringatom.
 12. The condensed cyclic compound of claim 1 represented by one ofFormulae 1A to 1D:

wherein, in Formulae 1A to 1D, ring A₁ and ring A₂ are eachindependently selected from a phenyl group, a dibenzofuranyl group, anda dibenzothiophenyl group, L₁ is selected from groups represented byFormulae 3-15, 3-28, 3-41, and 3-51, L₂ and L₃ are each independentlyselected from groups represented by Formulae 3-1, 3-15, 3-28, 3-41, and3-51, a1 to a3 are each independently selected from 0, 1, and 2, R₁ toR₇, R₁₁ to R₁₈, R₃₁, and R₃₂ are each independently selected from ahydrogen, a deuterium, —F, a cyano group, a C₁-C₁₀ alkyl group, and aC₁-C₁₀ alkoxy group; a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group,each substituted with at least one selected from a deuterium, —F, and acyano group; a phenyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinylgroup, a dibenzofuranyl group, and a dibenzothiophenyl group, eachsubstituted with at least one selected from a deuterium, —F, a cyanogroup, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₂₁)(Q₂₂)(Q₂₃);and—Si(Q₁)(Q₂)(Q₃), wherein Q₁ to Q₃ and Q₂₁ to Q₂₃ are each independentlyselected from a hydrogen, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, aphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group,a dibenzofuranyl group, and a dibenzothiophenyl group, b1 and b2 areeach independently 0 or 1, c1 is 1 or 2, and c2 is 0, 1, or 2

wherein, in Formulae 3-1, 3-15, 3-28, 3-41, and 3-51, Y₁ is selectedfrom O, S, and C(Z₃)(Z₄), Z₁ to Z₄ are each independently selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃),wherein Q₁₁ to Q₁₃ are each independently selected from a hydrogen, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a fluorenyl group, adibenzofuranyl group, and a dibenzothiophenyl group, d4 is an integerselected from 0 to 4, d3 is an integer selected from 0 to 3, and * and*′ are each a binding site to a neighboring atom.
 13. The condensedcyclic compound of claim 12, wherein a group represented by

is selected from groups represented by Formulae 5-1 to 5-3, 5-31, 5-39,5-47, and 5-55, and a group represented by

is selected from groups represented by Formulae 5-1 to 5-3, 5-31, 5-39,5-47, 5-55, 5-61, 5-63, 5-65, 5-67, and 5-69:

wherein * is a binding site to a neighboring atom.
 14. The condensedcyclic compound of claim 1, being one of Compounds 1 to 271:


15. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer and at least one condensed cyclic compound representedby Formula 1 of claim
 1. 16. The organic light-emitting device of claim15, wherein the first electrode is an anode, the second electrode is acathode, and the organic layer comprises: i) a hole transport regiondisposed between the first electrode and the emission layer, wherein thehole transport region comprises a hole injection layer, a hole transportlayer, an electron blocking layer, or any combination thereof; and ii)an electron transport region disposed between the emission layer and thesecond electrode, wherein the electron transport region comprises a holeblocking layer, an electron transport layer, an electron injectionlayer, or any combination thereof.
 17. The organic light-emitting deviceof claim 15, wherein the emission layer comprises the condensed cycliccompound represented by Formula
 1. 18. The organic light-emitting deviceof claim 15, wherein the emission layer comprises the condensed cycliccompound represented by Formula 1 and a phosphorescent dopant, whereinan amount of the condensed cyclic compound is greater than an amount ofthe phosphorescent dopant.
 19. The organic light-emitting device ofclaim 17, wherein the emission layer emits blue light.
 20. The organiclight-emitting device of claim 15, wherein the emission layer comprisesthe condensed cyclic compound represented by Formula 1, and wherein thecondensed cyclic compound represented by Formula 1 is a thermallyactivated delayed fluorescence emitter.